Methane → 7,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

HRID 1196231Notes

Reaction equation

HRID 1196231 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.[ClH:30].C>CO>[ClH:30].[C:24]1([C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]3[CH:15]([CH2:16][NH:8][CH2:9]3)[C:14](=[O:17])[CH2:13][CH2:12]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 19384608(3aRS, 7aRS)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone

Product 1

HCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3aRS,7aRS)-2-Benzyl-7,7-diphenylperhydro-4-isoindolone (150 g), methanol (1500 cc) and 1N hydrochloric acid (450 cc) are added to palladinized charcoal (10% palladium) (15 g); the reaction mixture is hydrogenated with stirring at room temperature and at atmospheric pressure. After 5 hours' reaction, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered, then concentrated to dryness under reduced pressure (2.7 kPa); the residue is crystallized in ethanol (200 cc). The crystals obtained are drained, washed with ethanol (50 cc) and dried. (3aRS,7aRS)-7,7-Diphenylperhydro-4-isoindolone hydrochloride (110 g), m.p. 270° C. with decomposition, is obtained.

Workup

  1. customAfter 5 hours' reaction
  2. customthe theoretical volume of hydrogen has been absorbed
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customthe residue is crystallized in ethanol (200 cc)
  6. customThe crystals obtained
  7. washwashed with ethanol (50 cc)
  8. customdried

Sources & evidence

ORD record
ord-b8de1dae40df4967b272c275f674db3a
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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